Basic derivatives of iminodibenotl



Patented Apr. 6, 1954 UNITED STATES PATENT OFFICE BASIC DERIVATIVES OFIMINODIBEN ZY L Franz Hilfiger and Walt er Schindler, Basel,Switzerland, assignors to J. R. Geigy A. G., Basel,

Switzerland,

a Swiss firm No Drawing. Application January 22, 1953, Serial No.332,750

Claims priority, application Switzerland January 25, 1952 4 Claims. 1This invention concerns new basic derivatives of iminodibenzyl of thegeneral formula:

with N-(2.3-epoxy-propy1)-iminodibenzyl of the formula:

C H2--- H: L (j wherein Am has the meaning given above. The reaction cantake place in the presence or absence of solvents, with advantage in thewarm. The reactions are performed under normal pressure for example atthe boiling temperature of the amine or of the solvent, as which ethanoland methanol can be named, according to the reactive qualities andboiling point of the amine or of the solvent used, or they can beperformed at higher temperatures in autoclaves.

As starting materials of the formula Am-I-I can be named, for example:methylamine, ethylamine, n-propylamine, n-butylamine, dimethylamine,methyl-ethylamine, diethylamine, di-npropylamine, di-n-butylamine,methyl-n-butylamine, pyrrolidine and piperidine.

N-(2.3 epoxy-propyl) iminodibenzyl can be produced for example byreacting an alkali metal 2 compound, e. g. the sodium or lithiumcompound of iminodibenzyl with epichlorohydrin.

The new hydroxydiamine compounds form monoacid salts with inorganic andorganic acids; some of the salts are easily soluble in water.

The following examples illustrate the production of the compoundsaccording to the present invention. Parts are given as parts by weightand their relationship to parts by volume is as that of grammes to cubiccentimetres. The temperatures are in degrees centigrade.

EXAMPLE 1 Hydrochloride of N-(3-methyZamino-2-hydroacypropyl)-z'mz'nodiben2yl 10 parts of iminodibenzyl and 5 parts ofepichlorohydrin are dissolved in parts by volume of abs. benzene and areheated to about 40-50. 2 parts of sodium amide suspended in toluene areadded while stirring vigorously. The temperature rises to whereupon thewhole is boiled for a further 6 hours under reflux. After 0001- ing,water is added to decompose the product, the benzene solution is washed,dried and evaporated. On distilling off the residue, N-(2.3-epoxy-propyl) -iminodibenzyl is obtained.

B. P.n.2165166 It can be recrystallised from benzine; M. P. '13-'74".

5 parts of N-(2.3-epoxy-propyl) -iminodibenzy1 are heated in anautoclave to with a 20% solution of methylamine in ethanol. After cool--ing, the excess methylamine and the ethanol are evaporated in thevacuum. The residue is taken up in ether and the hydrochloride isprecipitated by the addition of abs. alcoholic hydrochloric acid. It canbe recrystallised from abs. alcohol and melts at -191".

EXAMPLE 2 Hydrochloride of N-(3 dimethylamz'no 2 hydroxypropyl)-z'minodibenzyl 10 parts of the epoxy compound produced according toExample 1 are heated in a steel autoclave to 1l0-115 with 60 parts byvolume of a 20% solution of dimethylamine in methanol. After cooling,the volume is reduced in the vacuum, the residue is dissolved in 15%hydrochloric acid and any cloudiness is removed by ethering out. Theclear acid solution is made alkaline and the base which precipitates isethered out. The hydrochloride is precipitated by the addition ofalcoholic hydrochloric acid to the ether solution. It is recrystallisedfrom isopropanol and melts at 212-213".

EXAMPLE 3 Hydrochloride of N-(3-diethylamine-Z-hydromypropyl)-iminodibenzyl Hydrochloride of N-(3-pyrrolidino-2-hydroxypropyl)-iminodibenzyl M. P. 248-250", decomposition,

Hydrochloride of N-(3-piperidino 2 hydroxypropyD-iminodibenzyl, M. P.260,

Hydrochloride of N-(dipropylamino-2-hydroxypropyl) iminodibenzyl,

Hydrochloride of N-(ethylamine-2-hydroxypropyl) -iminodibenzyl,

Hydrochloride of N-(butylamino-2-hydroxypropyl) -iminodibenzyl.

What we claim is: 1. An N-(3-amino-2-hydroxypropyl) -iminodibenzylcorresponding to the formula:

wherein Am represents a member selected from the group consisting of lowmolecular alkyl- 15 amino radicals, low molecular dialkylamino radicalsand cyclic alkylene-imino radicals with 5 to 6 ring members.

2. An N-(3-amino-2-hydroxypropyl) -iminodibenzyl corresponding to theformula:

20 Gin-CH,

CED-CH:

3. N-(3-dimethylamino 2 hydroxypropyhiminodibenzyl.

4. N-(3 diethylamino-Z-hydroxypropyl) -iminodibenzyl.

No references cited.

1. AN N-(3-AMINO-2-HYDROXYPROPYL) -IMINODIBENZYL CORRESPONDING TO THEFORMULA: